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#4: Portland, Maine -- From ornate mansions to ocean views, this charming city—Maine's largest—will enchant you. Saunter down the brick sidewalks and cobblestone streets of the revitalized Old Port District, where you can browse through bookstores, explore craft shops and eat to your heart's content. Take to the waves on a scenic cruise or whale watch or hop a ferry to the islands in Casco Bay. At the end of the day, unwind at one of the city's brewpubs.